PRODUCTS

ESTRAGOLE

Estragole = Butyrophenone = Methyl Chavicol

CAS No.: 140-67-0
EC Number: 205-427-8
Pubchem CID : 8815
ECHA InfoCard: 100.004.935
ChemSpider ID: 13850247
Chemical formula: C10H12O
Molar Mass : 148.20 g/mol
MELTING POINT : 216 °C
Density: 0.946 g/cm3

Other names

1-Methoxy-4-(2-propenyl)-benzene
1-Allyl-4-methoxybenzene
Estragol
Estragon
p-Allylanisole
Chavicyl methylether
Methylchavicol
Chavicol methylether
Isoanethole
4-Allylanisole

Preferred IUPAC name
1-Methoxy-4-(prop-2-en-1-yl)benzene

Estragole (p-allylanisole, methyl chavicol) is a phenylpropene.
Estragole is a natural organic compound.
Estragoles chemical structure consists of a benzene ring substituted with a methoxy group and an allyl group.
Estragole is an isomer of anethole, differing with respect to the location of the double bond.

Estragole is a colorless liquid.
Although impure samples can appear yellow.
Estragole is a component of various trees and plants, including turpentine (pine oil), anise, fennel, bay, tarragon, and basil.
Estragole is used in the preparation of fragrances.

Estragole is an olefinic compound.
Estragole is a natural product found in Vitis rotundifolia, Pinus sylvestris var. hamata, and other organisms with data available.
C10H12O is a molecular formula of the Estragole.
The compound is named for estragon, the French name of tarragon.

Estragole other famous name is p-allylanisole or methyl chavicol.
Estragole is a natural organic compound.
Estragoles chemical structure consists of a benzene ring substituted with a methoxy group and a propenyl group.

Estragole is a double-bond isomer of anethole.
Estragole is a colorless to pale yellow liquid.
Estragole is the primary constituent of tarragon oil making up 60–75% of the oil.
Estragole is also found in basil (23–88%), pine oil, turpentine and Syzygium anisatum.

Estragole (4-Allylanisole), a relatively nontoxic volatile terpenoid ether.
Estragole is a major component of the essential oil of many plants.
Estragole dose-dependently blocks nerve excitability.
Estragole displays anti-toxoplasma activity.

Production
Hundreds of tonnes of basil oil are produced annually by steam distillation of Ocimum basilicum (common basil).
This oil is mainly estragole.But also contains substantial amounts of linalool.
Estragole is the primary constituent of essential oil of tarragon (comprising 60–75%).
Estragole is also present in pine oil, turpentine, fennel, anise (2%), Clausena anisata and Syzygium anisatum.

Estragole is used in perfumes.
Estragole is restricted in flavours as a biologically active principle:
Estragole can only be present in a flavour by using an essential oil.
Upon treatment with potassium hydroxide, estragole converts to anethole.
A known use of estragole is in the synthesis of magnolol.

Risks of the Estragole
Estragole is suspected to be carcinogenic and genotoxic, as is indicated by a report of the European Union.
A reduction of Estragole in consumption is thus indicated.
Special care of Estragole is also to be taken with infant nourishment, since many teas or tea-like beverages contain estragole.

Safety of the Estragole
Estragole is suspected to be carcinogenic.
Estragole is a genotoxic.

Firefighting of the Estragole
Fires involving this compound should be controlled using a dry chemical, carbon dioxide, foam or halon extinguisher.

Non-Fire Response of the Estragole
SMALL SPILLS AND LEAKAGE: If you spill this chemical, use absorbent paper to pick up all liquid spill material.
Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal.
Solvent wash all contaminated surfaces with alcohol followed by washing with a strong soap and water solution.
Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

STORAGE PRECAUTIONS: You should store this material in a refrigerator.

Protective Clothing of the Estragole
RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter.

First Aid of the Estragole
EYES: First check the victim for contact lenses and remove if present.
Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center.
Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician.
IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing.
Gently wash all affected skin areas thoroughly with soap and water.
If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.

INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air.
If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital.
Provide proper respiratory protection to rescuers entering an unknown atmosphere.
Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.

INGESTION: DO NOT INDUCE VOMITING.
If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center.
Be prepared to transport the victim to a hospital if advised by a physician.
If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body.
DO NOT INDUCE VOMITING.
IMMEDIATELY transport the victim to a hospital.

Physical Description
Estragole is a colorless liquid with odor of anise.
Estragole is an insoluble in water.
Estragole is isolated from rind of persea gratissima grath.
Estragole is isolated from oil of estragon.
Estragole found in oils of Russian anise, basil, fennel turpentine, tarragon oil, anise bark oil.

Estragole is a liquid.
Estragole is a colorless to light yellow liquid.
Estragoles odor reminiscent of anise with a corresponding sweet taste.
Estragoles sweet taste reminiscent of anise.
Estragoles boiling point is 421 °F .

Estragoles flash point is 178 °F.
Estragole is very soluble in ethanol, chloroform.
Estragoles density is 0.9645 at 70 °F.

Estragoles vapor pressure is 0.05 mmHg.
Estragoles log kow values is 3.47.
Estragoles Henrys Law Constant value is 4.62X10-4 atm-cu m/mol at 25 °C.
Estragole is stable under recommended storage conditions.

Estragole is hazardous decomposition products formed under fire conditions.
Because the Carbon oxides.
Estragoles specific gravity is 0.9645 at 21 °C.
Estragoles Hydroxyl radical reaction rate constant is 5.43X10-11 cu cm/molec-sec at 25 °C.
Estragoles Ozone reaction rate constant is 1.2X10-17 cu cm/molec-sec at 25 °C.

Absorption, Distribution and Excretion of Estragole
Approximately 20% of a dose of estragole, a naturally occurring flavoring agent, was excreted in the urine.

Air & Water Reactions of Estragole
Forms azeotropic mixtures with water.

Fire Hazard of Estragole
This compound is combustible.

Health Hazard of Estragole
ACUTE/CHRONIC HAZARDS: Estragole is an irritant.

Reactivity Profile of Estragole
Estragole may react vigorously with strong oxidizing agents.
Estragole can react exothermically with reducing agents (such as alkali metals and hydrides) to release gaseous hydrogen.
Estragole may react exothermically with both acids and bases.

Belongs to the Following Reactive Group(s) of Estragole
Ethers
Hydrocarbons, Aliphatic Unsaturated

Potentially Incompatible Absorbents of Estragole
Use caution: Liquids with this reactive group.

Estragole occurs naturally in many culinary herbs, including anise, star anise, basil, bay, tarragon, fennel, and marjoram.
Widespread human exposure to estragole occurs through the consumption of these herbs and through the use of the oils derived from them as flavors and fragrances in numerous foods, cosmetics, and other consumer products.
Estragole is a constituent of turpentine oil, and indoor air exposure may result from the use of turpentine oil in furniture and other wood treatments.
Estragole occurs naturally in many common plants including anise, star anise, basil, bay, tarragon, fennel, marjoram, and is also present in American wood turpentine oil.

Estragole is present in considerably higher concentrations in volatile oils derived from these plants and trees.
Flavor and fragrances containing estragole are used in numerous foods and food products, perfumes, soaps, and detergents.
The Flavor and Extract Manufacturer’s Association , noting a wide range of exposures, estimated several years ago that daily per capita consumption of estragole in the U.S. was 70 mg.
The U.S. Department of Food and Agriculture lists the status of estragole along with many essential oils containing estragole (e.g., extracts of anise, basil, bay leaves, tarragon and fennel) as “generally recognized as safe” (GRAS) for food use.
Estragole may occur in indoor air because of wood treated with turpentine oil. Because it is a minor constituent of tobacco smoke.

General description of Estragole
Estragole is a plant extract, used in a variety of consumer products including flavorings, perfumes and homeopathic remedies.
Estragole exists as a natural constituent in a variety of plants and their essential oils, including, sweet basil, sweet fennel, tarragon and Croton zehntneri which are used in food products as flavoring agents.

Application of Estragole
Estragole may be used as an analytical reference standard for the quantification of the analyte in food products.
Estragole may be used as an Croton zehntneri aromatic plant, pharmaceutical products, herbal teas.
Estragole used for herbal extracts using gas chromatography coupled with flame ionization detection (GC-FID) and gas chromatography coupled to mass spectrometry (GC-MS).

Use and Manufacturing of Estragole
fragrance as 4- allylanisole
fragrance component
other chemicals (function unknown)

Estragole naturally occurs in tarragon oil, basil oils, anise bark oil, and others; Used as a flavoring ingredient and a fragrance in perfumes and soaps.
Estragole used for in perfumes and as flavor in foods and liqueurs.

Food Category:
Alcoholic beverages
Baked goods
Chewing gum
Condiments, relishes
Fats, oils
Frozen dairy
Gelatins, puddings
Hard candy
Meat products
Nonalcoholic beverages
Soft candy

CAS-No.: 140-67-0
1407-27-8
77525-18-9
The scope of this Standard includes, but is not limited to the CAS number(s) indicated above; any other CAS number(s) used to identify this fragrance ingredient should be considered in scope as well.

Estragole (4-allyl anisole,1-methoxy-4-enylbenzene) is a naturally occurring compound which can be extracted from Anise, Star Anise, Fennel and Basil.
Flavors and fragrances containing estragole are used in food products, perfumes, soaps and detergents.
The Flavor and Extract Manufacturers Association (FEMA) noted that the estimated daily exposure of estragole in USA was found to be 70 µg/ capita consumption.

Anise and Star Anise (also known as Anise seed, Sweet Cumin Illicium, Chinese Anise, Chinese Star Anise) contain about 1-4% volatile oil, estragole constitutes the main component.
Anise and Star Anise oils are used in pharmaceuticals and cosmetic products, they also used as stimulants and expectorants.
Star Anise is used to Estragole in Chinese Medicine for the same biological properties.

Storage Temperature of the Estragole is +5°C.
Estragole is sweet phenolic anise harsh spice green herbal minty herbaceous-sweet like-anethole-less-sweet sweet-herbaceous anise-fennel fougere lavender chypre pinelilac appleblossom heliotrope sweet-pea.

The odour and uses of Estragole
Odour=> sweet phenolic anise harsh spice green herbal minty herbaceous-sweet like-anethole-less-sweet Sweet-herbaceous Anise-Fennel type odor

Perfume-Uses=> Fougere Lavender Chypre PineLilac Appleblossom Heliotrope Sweet-Pea Bay Green Basil Rootbeer Cananga Herbal-types, Fougeres, Lavender, Chypre, Pine, Soap-perfumes, Floral-types, Lilac, Appleblossom, Heliotrope, As-Modifier, Woody-blends,
Spice Herb Sauces Licorice Liqueurs Candy, Meat, Licorice, Spice, Fruit-flavour, Baked-foods, Chewing-gum.

Blends-well-with=> Methyl Chavicol, Herbaceous-notes, Gums

Estragole caused contractions of isolated frog muscles followed by relaxation.
This effect was reduced in potassium-depolarized muscles or in the presence of quinidine or manganese.
Estragole appears to cause these effects by producing a persistent depolarization of the muscle membrane.

Estragole was found to be strongly active in prolongation of hexobarbital narcosis and zoxazolamine paralysis following intraperitoneal doses of 2.5, 10, 40, 160 and 640 mg/kg in mice.
This implies that it inhibits hepatic microsomal enzyme functions.

Estragole, a volatile phenylpropanoid contained in a variety of edible herbs, has been demonstrated to be genotoxic and carcinogenic.
Estragoles addition as a flavoring substance to foodstuffs has been banned by the regulatory bodies of the European Union.
Fast and accurate analytical methods for Estragoles determination in herbs are thus necessary to assess the dietary exposure of this substance in humans and, in particular, to sensitive groups.

Headspace solid-phase microextraction (HS-SPME) combined with gas chromatography–mass spectrometry (GC–MS) was applied for determination of estragole in infusions from different widely used commercial herbal teas based on Foeniculum vulgare (fennel) seeds.
The optimized HS-SPME extraction conditions involved the use of a polydimethylsiloxane fiber exposed to the herbal infusion for 20 min at 50°C followed by GC–MS analysis.
The method was fully validated for linearity, sensitivity, accuracy, and precision and applied to real samples; the level of estragole in infusions of commercial fennel seed teas was found to be within 50–250 µ`−1.

Since estragole has been described as potent carcinogen and did not show any flavour impact on the odour of fennel, the flavour of anise and tarragon was examined by combinations of instrumental and sensory analyses.
In anise fruits, trans-anethole, 2-isopropyl-3-methoxypyrazine, and anisaldehyde showed high flavour dilution (FD) factors, followed by those of eugenol, cis-anethole, estragole and linalool.
Quantitation of the odorants showing higher FD factors in anise tea, and calculation of odour activity values (OAVs) by dividing the concentrations of the respective compound by its recognition threshold in water revealed the highest OAV for trans-anethole, followed by those of anisaldehyde and estragole.

Estragole, also known as p-allylanisole, chavicol methyl ether, and methyl chavicol has the structural formula l OCHs and is a colorless liquid having a characteristic somewhat sassafrassy odor and flavor. Estragole is used in the manufacture of perfumes and flavors. Heretofore, estragole for these uses has been obtained from estragon oil, also known as tarragon oil, whereof estragole is the chief contributor of the oils odor and flavor.
Estragole is a constituent of turpentine extracted from a living pine tree and is a constituent of volatile products extracted from dead pine stumps by steam distillation, for example.
Estragole is also a constituent of the distillation residues of crude sulfate turpentine. Refined sulfate turpentine and other pinene-containing products are obtained on a large commercial scale by distilling the crude sulfate turpentine evolved during the digestion of southern pine wood by the kraft process in which a cooking liquor containing sodium hydroxide and sodium sulfide is used. The residues from this distillation contain higher boiling terpenes and non-terpenes of potential commercial value, among which is estragole.
Estragole rich (90%-95% by weight) fractions can be obtained economically from any of the above sources by distillation techniques. These fractions will contain also terpene alcohols and terpene ketones, normal constituents of the volatile products of the pine tree, which have boiling points relatively close to that of estragole (216 C.). These terpene alcohols and terpene ketones have a strong pine oil odor and flavor which tend to distort the odor and flavor of estragole. It is exceedingly difficult to remove these undesirable odor and flavor imparting impurities from estragole rich fractions by rectification-techniques.
This invention is directed to a novel method of preparing an essentially pure estragole fraction from pine sources, which fraction is substantially free of odor and flavor distorting impurities.

Separation of the liquid phase from the estragole crystals can be accomplished by any convenient means such as by centrifugation, filtration and decantation. The separated estragole crystals have, adhering to their surface, a layer of the liquid phase from which they were separated. This liquid phase layer contains impurities present in the original feed stock. To remove this adhering liquid and thus to improve further the purity of the estragole, the separated estragole crystals can be washed with a cold liquid.
Another suitable method for removing undesired adhering liquid from the surface of estragole crystals is to allow the estragole crystals to slowly melt, the melted estragole acting as the wash liquid. If this method is employed, the separation process (centrifugation, decantation, filtration) is continued at recurring time intervals or preferably continuously to remove melted estragole which carries with it impure adherent liquid phase.
The degree of purity of the estragole obtained in practicing the method of this invention will depend on the thoroughness of the separation of the liquid phase from the estragole crystals. Purity of estragole obtained using this process will range from about 97% to about 99.9+% by weight estragole.

Estragole (EG) is biosynthesized in herbs including anise, basil, bay, tarragon, fennel and marjoram, and is thought to be a useful biomass for the food and health industries. Moreover, the metabolites from estragole are useful intermediates in organic synthetic chemistry. However, estragole has been transformed only by chemical methods

Estragole is a particular metabolite which belongs to the class of phenylpropanoids that can be found in the essential oil of Agastache foeniculum. Estragole with lipophilic nature was emulsified in glycerol monostearate (GMS) emulsifier.
Estragole is a known attractant of the African oil palm weevil (Elaeidobius kamerunicus), which pollinates oil palms (Elaeis guineensis). There has been recent interest in the biogenic emissions of estragole but it is normally not included in atmospheric models of biogenic emissions and atmospheric chemistry despite its relatively high potential for secondary organic aerosol formation from photooxidation and high reactivity with OH radical.

Estragole is naturally found in turpentine, basil and tarragon oil. It appears colorless to pale yellow clear liquid with licorice and phenolic odor.
Estragole is used in the preparation of fragrance.

APPLICATIONS & USES
1. used in fragrance compositions such as lavender, fougere, and chypre
2. used as perfuming agents, effective in creating an absinthe accord, provide a boost to wormwood notes
3. used in the ingredient of local anesthetic
4. used as intermediate of medicine, having wide spread applications in folk medicine and aromatherapy
5. used as food additives

Packaging
Packed in 25/50/200kg Drum

Estragole is a component of several herbs such as tarragon, basil, fennel, and anise.
Of these, the fruits of fennel and anise serve as remedy against catarrh of the respiratory tract and gastro-intestinal disorders.
Therefore, fennel extractions are the classical tea for nursing babies to prevent flatulence and spasms.
However, estragole as a ring-substituted allylbenzene along with the structurally similar safrole has been reported as a potent carcinogen in rodents .
The reason for their hepatoxic properties is a specific metabolism of allylbenzenes leading to 1 - hydroxylation of the side chain.

Estragole causes cancer in animals and may cause cancer in humans.
Estragole is used as a flavor additive in foods, and as a fragrance in cleaning agents and cosmetic products.
Methyl chavicol (estragole) is a natural organic compound.
Estragoles chemical structure consists of a benzene ring substituted with a methoxy group and a propenyl group.

As noted in a report by the European Union Herbal Medicinal Products Committee, estragole is suspected to be carcinogenic and genotoxic.
Several studies have clearly demonstrated that the metabolism, metabolic activation, and covalent binding profiles are dose-dependent, and their relative importance is markedly reduced at low exposure levels (ie, these events are not linear with respect to dose).
In particular, rodent studies suggest that these events are probably minimal in the dose range of 1-10 mg/kg body weight, which is approximately 100 to 1,000 times the human exposure to this substance.
For these reasons, it was concluded that the current exposure to estragol from the consumption of herbal medicinal products (short-term use in adults at the recommended posology) does not pose a significant cancer risk.
Meanwhile, estragole exposure to vulnerable groups such as young children, pregnant and lactating women should be minimized.

The Scientific Committee on Food from the Directorate of Health and Consumer Protection took a position of concern and concluded that "Estragole has been shown to be genotoxic and carcinogenic. Therefore, the existence of a threshold is unacceptable and the Committee was unable to establish a safe exposure limit. As a result, reductions in exposure and restrictions on use levels were noted. "

Methyl chavicol (estragole) is a double-bond isomer of anethole.
Estragole is a colorless to pale yellow liquid.
Estragole is the primary constituent of essential oil of tarragon, making up 60–75% of the oil.
Estragole is also found in essential oils of basil (23–88%), pine oil, turpentine, fennel, anise (2%), and syzygium anisatum.

Estragole is a component of fennel essential oil and its consumption seems to be a potential health risk according to most recent statements.
The use of fennel tea in the recommended doses should be hardly dangerous because the essential oil of the fennel cultivars currently cultivated in Germany contains only 2.5% estragole among numerous other components.
Nevertheless, ail available means should be exploited to decrease the estragole content in fennel.
The analysis of 233 populations consisting of 8490 individual fruit samples ascertained a high natural variability of the estragole content as prerequisite of breeding estragolereduced new cultivars.
Whereas low estragole content coincided prevalently with high contents of essential oil and fenchone, breeding of estragole reduced cultivars with trans-anethole content of at least 60% as required by the pharmacopoeia seems to be difficult due to the strong positive correlation between the estragole and trans-anethole content in the essential oil.

Estragole has C10H12O molecular formula, 148,20 g/mol molecular weight, 216°C boiling point at 760 mmHg, 0,946 g/cm3 density, liquid form in room temperature, and has an optic inactive characteristic .
This compound is an alilfenol derivate compound that is formed by shikimat pathway (fenilpropanoid) and can be isomerized to form anethole.

There are several researches on estragole isomerization that have been conducted.
studied catalytic isomerization of estragole to anethole over hydrotalcites and HT-like compounds.
Risnayeti and Mas’ud (1997) studied estragole isomerization mechanism using combined methode of site-specific natural isotropic fractionation and nuclear magnetic resonance.

Estragole, a common component of herbs and spices, is a wellknown genotoxic hepatocarcinogen in rodents, whereas its potential toxic effect in humans is still debated.
In the European contest, one of the major sources of human exposure to this phytochemical is Foeniculum vulgare Mill.
Therefore, the aim of this study was to evaluate the in vitro toxicity of estragole in the context of two complex phytochemical mixtures derived from fennel: fennel seed powder (FSPw) and fennel seed essential oil (FSEO).

The estragole-containing preparations were analysed for their ability to cause cytotoxicity, genotoxicity, apoptosis and cell cycle perturbation in the human hepatoma (HepG2) cell line.
None of the tested concentrations of FSPw induced DNA damage, nor apoptosis or cell cycle perturbation.
Although FSEO did not induce any genetic damage as well, it exerted marked dose-dependent apoptotic effects on HepG2 cells with a concurrent cell cycle arrest in G2/M at the highest tested dose.
Although prospective analyses are required to clarify the observed toxic effects of FSEO, our results support the hypothesis that the genotoxicity of estragole may be significantly reduced or null in the context of botanical mixtures.

Description of Estragole
Estragole is a phenylpropene, a natural organic compound.
Its chemical structure consists of a benzene ring substituted with a methoxy group and a propenyl group.
It is a double-bond isomer of anethole.

Estragole is the primary constituent of essential oil of tarragon.
Estragole is also found in essential oils of basil, pine oil, turpentine, fennel, anise, and Syzygium anisatum.
Estragole is used in perfumes and as a food additive for flavor.

Chemical Structure Description of Estragole
A chemical structure of a molecule includes the arrangement of atoms and the chemical bonds that hold the atoms together.
The Estragole molecule contains a total of 23 bond(s) There are 11 non-H bond(s), 7 multiple bond(s), 3 rotatable bond(s), 1 double bond(s), 6 aromatic bond(s), 1 six-membered ring(s) and 1 ether(s) (aromatic).

Chemical Properties of Estragole
Appearance :    Colourless liquid
Boiling Point   : 216 °C
CAS Number : 140-67-0
ChEBI   : 545613
Density :   0.946 g/cm3
EINECS Number   : 205-427-8
IUPAC Name   : 1-Allyl-4-methoxybenzene
InChI   : 1S/C10H12O/c1-3-4-9-5-7-10(11-2)8-6-9/h3,5-8H,1,4H2,2H3
InChIKey :    ZFMSMUAANRJZFM-UHFFFAOYSA-N
Molar Mass :    148.20 g/mol
Molecular Formula :    C10H12O
RTECS Number :    BZ8225000
Refractive :    n20/D 1.521
Synonyms :    1-Methoxy-4-(3-propenyl)-benzene;Estragol;Estragon;p-Allylanisole;Chavicyl Methylether;Methylchavicol;Chavicol Methylether;Isoanethole;4-Allylanisole

General description of Estragole
Estragole is a plant extract, used in a variety of consumer products including flavorings, perfumes and homeopathic remedies.
This compound exists as a natural constituent in a variety of plants and their essential oils, including, sweet basil, sweet fennel, tarragon and Croton zehntneri which are used in food products as flavoring agents.

Application of the Estragole
Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique.
Contact Technical Service for further support.
Estragole may be used as an analytical reference standard for the quantification of the analyte in food products, Croton zehntneri aromatic plant, pharmaceutical products, herbal teas and herbal extracts using gas chromatography coupled with flame ionization detection (GC-FID) and gas chromatography coupled to mass spectrometry (GC-MS).

Estragole, a relatively nontoxic terpenoid.
Estragole is an important constituent of many essential oils with widespread applications in folk medicine and aromatherapy and known to have potent local anesthetic activity.

Estragole (4-Allylanisole), a relatively nontoxic volatile terpenoid ether, is a major component of the essential oil of many plants.
Estragole has potent local anesthetic activity and dose-dependently blocks nerve excitability.
Estragole displays anti-toxoplasma activity.

Storage of the Estragole
Please store the product under the recommended conditions in the Certificate of Analysis.

FIRST AID MEASURES of Estragole
Inhalation
In case of inhalation, move the victim to fresh air.
If breathing is difficult, put the victim on oxygen.
If breathing stops, carry out artificial respiration.

In case of skin contact
Wash thoroughly with water and soap.

In case of eye contact
Rinse well with plenty of water for at least 15 minutes.

Ingestion
Do not make an unconscious person vomit or swallow anything. Rinse the mouth thoroughly with water.

FIRE-FIGHTING MEASURES of Estragole
Extinguishing media
Carbon dioxide, dry powder.

Special hazards arising from the substance
Harmful/toxic vapours, carbon oxides may be released during the fire.

Advise for fire-fighters
Wear an autonomous breathing apparatus and suitable protection clothing against chemical agents.

ACCIDENTAL RELEASE MEASURES of Estragole
Personal precautions
Use personal protective equipment.
Evacuate the personnel from the contaminated zone.
Ensure adequate ventilation.

Environnemental precautions
Keeping away from drains, surface and ground waters.

Methods and materials for containment and cleaning up
Clean up without creating dust and place in adapted and sealed containers for elimination.
Wash the contaminated aera with water and soap.
Confine washing water and dispose of it complying with the local regulations.
After cleaning, quickly eliminate traces of water with a product absorbing liquids (for example : sand, sawdust, universal binder, Kieselguhr).

HANDLING AND STORAGE of Estragole
Precautions for safe handling
Avoid formation of dust.
Avoid contact with skin and eyes.
During handling, wear suitable personal protective equipment.
Follow the normal measures for preventive fire protection.

Specific handling
No data available.

Specific end use(s)
No data available.

Conditions for safe storage, including any incompatibilities
Store in a cool well-ventilated place.
Keep container tightly closed in a dry place away from light.
Estragole is store at <+8°C.

EXPOSURE CONTROL/PERSONAL PROTECTION of Estragole
Respiratory protection
Wear imperatively an appropriated mask/respirator, tested and approved by standards such as NIOSH (US) or CEN (EU).

Hand protection
Handle with protective gloves.
The selected gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it.

Eye protection
Wear safety glasses.

Skin protection
Wear suitable protective clothing according to the quantity and the level of activity of the substance at the workplace.

PHYSICAL AND CHEMICAL PROPERTIES of Estragole
Information on basic physical and chemical properties
Physical state : Liquid
Color : No data available.
Solubility in : Ethyl alcohol (Soluble)
Melting point : 216 °C
pH : No data available.
Partition coefficient: n-octanol/water No data available.
Auto-ignition temperature : No data available.
Decomposition temperature No data available.
Viscosity : No data available.
Initial boiling point : 214°C
Flash point : 81°C

STABILITY AND REACTIVITY of Estragole
Reactivity
No data available.

Chemical stability
Stable under recommanded storage conditions.
Estragole is a known attractant of the African oil palm weevil (Elaeidobius kamerunicus), which pollinates oil palms (Elaeis guineensis).
There has been recent interest in the biogenic emissions of estragole but it is normally not included in atmospheric models of biogenic emissions.
atmospheric chemistry despite Estragoles relatively high potential for secondary organic aerosol formation from photooxidation.
Estragole is high reactivity with OH radical.

reported the first direct canopy-scale measurements of estragole fluxes from tropical oil palms by the virtual disjunct eddy covariance technique and compare them with previously reported data for estragole emissions from Ponderosa pine.
Flowers, rather than leaves, appear to be the main source of estragole from oil palms; derived a global estimate of estragole emissions from oil palm plantations of ~0.5 Tg y−1.

The steam distillation of Ocimum basilicum (common basil) produces hundreds of tons of basil oil each year.
basil oil is mainly estragole, but also contains significant amounts of linalool.
The primary component of estragole is tarragon in essential oil (containing 60-75%).
Also present are pine oil, turpentine, fennel, anise (2% ), Clausena anisata and Syzygium anisatum.

Estragole is used in perfumes, and as a biologically active principle it has been restricted in flavors: it can only be found in a flavor using an essential oil.
Upon treatment with potassium hydroxide, it converts estragole to anethole.
One known use of estragole is in the synthesis of magnolol.
Possibility of hazardous reactions
No hazardous reactions during storage and handling complying with the instructions.

Conditions to avoid
No data available.

Incompatible materials
No data available.

Hazardous decomposition products
No hazardous decomposition products if the instructions for handling and storage are respected.
During high overheating of the substance or during a fire, hazardous decomposition products may be produced.

Estragole is also called methyl chavicol and is a phenylpropene.
Estragole is a natural organic compound.
Estragole is an isomer of anethole, differing with respect to the location of the double bond.

Sources:
Sweet Basil oil, Sweet fennel oil, Tarragon oil, Anis star oil, Anis vert oil.

Uses:
Estragole is commonly used in various Fragrance applications.
Estragole is also used in food and beverages.

Methyl chavicol, also called estragole or isoanethole, is a phenol methyl ether found in basil, fennel, ravensera, star anise, anise, and tarragon.
Methyl chavicol may be carcinogenic in high doses, and the IFRA has a limit on amounts permitted in products sold.
Certain chemotypes of basil, ravensara, and tarragon can have over 80% methyl chavicol.
With constituents of methylchavicol (47%), geranial (19%) and neral (15%), Ocimum basilicum (basil) oil had radical scavenging and antioxidant activities and may be usable in treating oxidative damage and stress from certain inflammatory conditions.

Both basil and its estragole constituent demonstrated anti-inflammatory activity, with the essential oil more effective than the constituent for acute and chronic anti-inflammatory action.
Basil (Ocimum basilicum) essential oil showed activity against eight important postharvest deteriorating fungi with the following constituents being significant: 1,8-cineole, linalool, camphor, α-terpineol, methyl chavicol, and eugenol.
Basil and tarragon essential oils containing estragole have been used since ancient times, with no real toxicity to humans or animals.

The main components of Basil essential oil are 74% estragole (methyl chavicol) and 19.5% linalool and the main components of Tarragon essential oil are 70% estragole and Trans and Cis-b-OCIMENE 25%.
Some species may have a higher percentage of estragole (>85%).
Tarragon oil, which contains basil essential oil and estragole, has been used since ancient times without showing any real toxicity to humans and animals.
Unfortunately, the high percentage of estragole has given these plants a bad reputation (dangerous, toxic, carcinogenic, not recommended in aromatherapy, etc.).

Methyl Chavicol or estragole are 'alkyl benzenes' along with safrole (from sassafras), methyl eugenol, anethole and elemycin.

Some of these compounds, including safrole, have been shown to be carcinogenic in some studies. This has led, for example, to allow safrole to be used in very small quantities in leftover foodstuffs and perfumes, or even banned altogether.

Estragole has also demonstrated a genotoxic signal in rodents and has been the subject of numerous studies.
But so far, no European or American government official has banned the use of estragole or the herbs, oils, dietary supplements, fragrances, and medicines containing it.
Relevant concentrations are considered too low to be genotoxic.

The food and beverage industry is growing rapidly. The demand for products that can enhance the taste of food in increasing with consumer demanding more variations in flavors. In order to meet the consumer's demand, the manufacturers are developing more number of products that can improve the flavor of food. One such product is Estragole. The estragole is a naturally occurring flavor in tarragon, anis vert, sweet fennel, anis star, sweet basil, and others. The estragole is also termed as Methyl Chavicol and is chemically named as 1-methoxy-4-prop-2-enylbenzene.

The estragole is derived from the fractional distillation of basil oil.
The estragole finds a wide number of applications.
It is used as a medicine to treat the reactions developed in humans due to biting of insects.
It is also used in pharmaceutical products, herbal teas, and extracts.

The estragole is highly soluble in alcohol and partially soluble in water.
Due to this, it is widely used in making herbal liqueurs to develop a taste in the drinks.
The odor is very pleasant.
The estragole is used to cure humans of itching developed due to biting of insects such as honey bees, snakes and others.

It is also used to cure vomiting and sickness.
Such factors are significantly driving the adoption of estragole in the market thereby driving its growth.
The estragole is used to get relief from gastrointestinal symptoms, respiratory tract symptoms, flatulence, colic spasm, and other symptoms.

The estragole has a wide range of applications across diversified industries. In the food industry, it is used for herbal, pickle, tomato and other applications. It is also used in a range of consumer goods. This has driven the adoption of estragole across the globe thereby driving the growth of estragole market.

The consumption of estragole is not suggested for a sensitive group of people such as pregnant women, young children and women’s who breastfeed.
This category of people caters a considerable share in the number of people who can consume estragole.
The cost of manufacturing or deriving estragole is also high.
Such factors are hampering the consumption of estragole which in turn is restraining the growth of the market.

Estragole
Substance identity

EC / List no.: 205-427-8
CAS no.: 140-67-0
Mol. formula: C10H12O

Hazard classification & labelling of Estragole
Warning! According to the classification provided by companies to ECHA in REACH registrations this substance is harmful if swallowed, is harmful to aquatic life with long lasting effects, causes serious eye irritation, is suspected of causing genetic defects, is suspected of causing cancer, may cause an allergic skin reaction and causes skin irritation.
At least one company has indicated that the substance classification is affected by impurities or additives.

About Estragole

Estragole is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 10 to < 100 tonnes per annum.
Estragole is used by consumers, by professional workers (widespread uses), in formulation or re-packing, at industrial sites and in manufacturing.

Consumer Uses of Estragole
Estragole is used in the following products:
biocides (e.g. disinfectants, pest control products),
washing & cleaning products,
air care products,
polishes and waxes,
perfumes and fragrances
cosmetics
personal care products.

Other release to the environment of Estragole is likely to occur from: indoor use as processing aid and outdoor use as processing aid.

Article service life of Estragole
ECHA has no public registered data on the routes by which this substance is most likely to be released to the environment.
ECHA has no public registered data indicating whether or into which articles the substance might have been processed.

Widespread uses by professional workers of Estragole
Estragole is used in the following products:
polishes and waxes,
washing & cleaning products,
biocides (e.g. disinfectants, pest control products)
cosmetics and personal care products.

Estragole is used for the manufacture of: .
Other release to the environment of Estragole is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners).

Formulation or re-packing of Estragole
Estragole is used in the following products:
air care products
biocides (e.g. disinfectants, pest control products)
polishes and waxes
washing & cleaning products.

Release to the environment of Estragole can occur from industrial use:
formulation of mixtures.

Uses at industrial sites of Estragole
This substance is used in the following products:
washing & cleaning products
biocides (e.g. disinfectants, pest control products)
metal surface treatment products.

Estragole is used for the manufacture of:
machinery and vehicles.
Release to the environment of this substance can occur from industrial use:
in processing aids at industrial sites
in the production of articles and of substances in closed systems with minimal release.

Manufacture of Estaragole
Release to the environment of Estragole can occur from industrial use:
manufacturing of the substance.

Substances predicted as likel as to meet criteria for category 1A or 1B carcinogenicity, mutagenicity, or reproductive toxicity,
Estaragole is with dispersive or diffuse use(s) where predicted likely to meet any classification criterion for health or environmental hazards,
Estaragole is where there is a nanoform soluble in biological and environmental media.
Estaragole indicated, in 2009, as being intended to be registered by at least one company in the EEA.
Estaragole which have been registered and can be placed on the EEA market by those companies with a valid registration.

Substances for which classification and labeling data have been submitted to ECHA in a registration under REACH or notified by manufacturers or importers under CLP.
Such notifications are required for hazardous substances, as such or in mixtures, as well as for all substances subject to registration, regardless of their hazard.

Butyrophenone

Substance identity
EC / List no.: 207-799-7
CAS no.: 495-40-9
Mol. formula: C10H12O

Hazard classification & labelling of Butyrophenone

Danger! According to the classification provided by companies to ECHA in CLP notifications this substance causes serious eye damage and may cause an allergic skin reaction.

Substances predicted as likely to meet criteria for category 1A or 1B carcinogenicity, mutagenicity, or reproductive toxicity, or with dispersive or diffuse use(s) where predicted likely to meet any classification criterion for health or environmental hazards, or where there is a nanoform soluble in biological and environmental media.
Substances indicated, in 2009, as being intended to be registered by at least one company in the EEA.

SYNONYM:

1-allyl-4-methoxybenzene
1-METHOXY-4-(2-PROPENYL)BENZENE
1-methoxy-4-(2-propenyl)benzene
1-methoxy-4-(prop-2-en-1-yl)benzene
1-methoxy-4-prop-2-enylbenzene
1-metoxi-4-prop-2-enylbenzene
4-Allylanisole
4-allylanisole
4-allylanisole
Basil essential oil
Basil oil
BASIL EO
BASIL EO VIETNAM
BASIL ESSENTIAL OIL
BASIL ESSENTIAL OIL VIETNAM
BASIL OIL
BASIL OIL (CHEMOTYPE ESTRAGOLE)
BASILIC VIETNAM HE
ESTRAGOLE
Estragole
METHYL CHAVICOL
Methyl Chavicol
OCIMUM BASILICUM OIL
Estragole
Butyrophenone
butyrophenone
Estragole
1-Butanone, 1-phenyl-
1-phenylbutan-1-one
BUTYROPHENONE
Butyrophenone
butyrophenone
4-Allylanisole
495-40-9
140-67-0
1-Allyl-4-methoxybenzene
p-Allylanisole
Methyl chavicol
Tarragon
Estragol
Chavicol methyl ether
Esdragol
Esdragole
Esdragon
Isoanethole
Anisole, p-allyl-
4-Methoxyallylbenzene
Terragon
p-Methoxyallylbenzene
1-methoxy-4-prop-2-enylbenzene
4-Allylmethoxybenzene
4-Allyl-1-methoxybenzene
Benzene, 1-methoxy-4-(2-propenyl)-
Methylchavicol
p-Allylmethoxybenzene
Chavicyl methyl ether
Chavicol, O-methyl-
3-(p-Methoxyphenyl)propene
1-METHOXY-4-(2-PROPENYL)BENZENE
1-allyl-4-methoxy-benzene
Methyl chavicole
NCI-C60946
UNII-9NIW07V3ET
MFCD00008653
1-Methoxy-4-(2-propen-1-yl)benzene
NSC 404113
3-(4-Methoxyphenyl)-1-propene
p-Allylphenyl methyl ether
Ether, p-allylphenyl methyl
9NIW07V3ET
CHEBI:4867
Benzene, 1-methoxy, 4-prop-2-enyl
Benzene, 1-methoxy-4-(2-propen-1-yl)-
DSSTox_CID_575
DSSTox_RID_75667
DSSTox_GSID_20575
Estragole (natural)
FEMA Number 2411
Allylphenyl methyl ether, p-
CAS-140-67-0
FEMA No. 2411
CCRIS 1317
HSDB 5412
EINECS 205-427-8
EPA Pesticide Chemical Code 062150
BRN 1099454
Isoanthethole
Esteragol
Methyl-Chavicol
AI3-16052
4-allylanisol
para-allylanisole
p-Allyl-Anisole
Chavicol, methyl-
O-Methyl-Chavicol
1-methoxy-4-(2-propenyl)-benzene
p-methoxy allylbenzene
4-methoxy allylbenzene
4-Allylanisole, 98%
Estragol (methylchavicol)
Methyl chavicole (estragole)
SCHEMBL57204
4-06-00-03817 (Beilstein Handbook Reference)
MLS001065575
Para-allylanisole (estragole)
Estragole, analytical standard
SPECTRUM1505117
WLN: 1U2R DO1
CHEMBL470671
DTXSID0020575
FEMA 2411
4-Allylanisole, >=98%, FCC
HMS2268E24
ZINC967635
4-Allylanisole, analytical standard
HY-N5060
Tox21_202387
Tox21_302930
NSC404113
s5339
1 -Methoxy-4-(2-propenyl) benzene
AKOS000121300
CCG-214642
NSC-404113
1-methoxy-4-(prop-2-en-1-yl)benzene
1-Methoxy-4-(2-propen-1-yl)-Benzene
1-Methoxy-4-(2-propenyl)benzene, 9CI
NCGC00091434-01
NCGC00091434-02
NCGC00091434-03
NCGC00256481-01
NCGC00259936-01
AS-35303
O080
SMR000112379
4-Allylanisole, purum, >=97.0% (GC)
A0702
CS-0032231
FT-0617414
BENZENE,1-ALLYL,4-METHOXY METHYLCHAVICOL
Q419495
SR-01000838348
BENZENE,1-ALLYL,4-METHOXY METHYLCHAVICOL
J-007415
SR-01000838348-2
p-allylanisole, 4-allyl-1-methoxybenzene, methyl chavicol
1407-27-8
77525-18-9